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Synlett 2005(16): 2469-2472  
DOI: 10.1055/s-2005-917079
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Ring-A-Substituted Tryptophan by a Palladium-Catalyzed Heteroannulation Reaction

Yanxing Jia, Jieping Zhu*
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: zhu@icsn.cnrs-gif.fr;
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Publikationsverlauf

Received 15 July 2005
Publikationsdatum:
21. September 2005 (online)

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Abstract

Coupling of substituted o-iodoanilines with methyl (S)-2-N,N-di-tert-butoxycarbonyl-5-oxo-pentanoate, derived from glutamic acid, in DMF in the presence of palladium acetate and DABCO provides substituted tryptophans in good to excellent yields.

Key words

palladium-catalyzed heteroannulation - indole synthesis - substituted tryptophan

    References

  • For examples, see:
  • 1a Hamaker LK. Cook JM. In Alkaloids: Chemical and Biological Perspectives   Vol 9:  Pelletiers SW. Elsevier Science; New York: 1995.  p.23-84  
    Google Scholar
  • 1b Lounasmaa M. Hanhinen P. Westersund M. In Alkaloids   Vol 52:  Cordell GA. Academic Press; San Diego: 1999.  p.103-195  
    Google Scholar
  • 2 Campagnuolo C. Fattorusso E. Taglialatela-Scafati O. Eur. J. Org. Chem.  2003,  284 
    CrossrefGoogle Scholar
  • 3a Raverty WD. Thomson RH. King TJ. J. Chem. Soc., Perkin Trans. 1  1977,  1204 
    CrossrefGoogle Scholar
  • 3b 6-Bromo d-hypa-phorine has also been isolated, see: Kondo K. Nishi J. Ishibashi M. Kobayashi J.-I. J. Nat. Prod.  1994,  57:  1008 
    CrossrefGoogle Scholar
  • 4 Kerr SJ. Armati PJ. Pemberton LA. Smythe G. Tattam B. Brew BJ. Neurology  1997,  49:  1671 
    Google Scholar
  • 5 Peterson AC. Migawa MT. Martin MJ. Hamaker LK. Czerwinski KM. Zhang W. Arend RA. Fisette PL. Ozaki Y. Will JA. Brown RR. Cook JM. Med. Chem. Res.  1994,  4:  531 
    Google Scholar
  • 6 Munn D. Zhou M. Attwood J. Bondarev I. Conway S. Marshall B. Brown C. Mellor A. Science  1998,  281:  1191 
    CrossrefGoogle Scholar
  • 7a Gouda H. Matsuzaki K. Tanaka H. Hirono S. Omura S. McCauley JA. Sprengeler PA. Furst GT. Smith AB. J. Am. Chem. Soc.  1996,  118:  13087 
    CrossrefPubMedGoogle Scholar
  • 7b For the total synthesis: Deng H. Jung J.-K. Liu T. Kuntz KW. Snapper ML. Hoveyda AH. J. Am. Chem. Soc.  2003,  125:  9032 
    CrossrefPubMedGoogle Scholar
  • 8 Kobayashi J. Suzuki H. Shimbo K. Takeya K. Morita H. J. Org. Chem.  2001,  66:  6626 
    CrossrefGoogle Scholar
  • 9 For a recent general review on the construction of indole ring, see: Gribble GW. J. Chem. Soc., Perkin Trans. 1  2000,  1045 
    CrossrefGoogle Scholar
  • 10a Allen MC. Brundish DE. Wade R. J. Chem. Soc., Perkin Trans. 1  1980,  1928 
    CrossrefGoogle Scholar
  • 10b Konda-Yamada Y. Okada C. Yoshida K. Umeda Y. Arima S. Sato N. Kai T. Takayanagi H. Harigaya Y. Tetrahedron  2002,  58:  7851 
    CrossrefGoogle Scholar
  • 11a Lee M. Philips RS. Bioorg. Med. Chem. Lett.  1992,  2:  1563 
    CrossrefGoogle Scholar
  • 11b Kaiser M. Groll M. Renner C. Huber R. Moroder L. Angew. Chem. Int. Ed.  2002,  41:  780 
    CrossrefGoogle Scholar
  • 12a Hino T. Taniguchi M. J. Am. Chem. Soc.  1978,  100:  5564 
    Google Scholar
  • 12b Taniguchi M. Anjiki T. Nakagawa M. Hino T. Chem. Pharm. Bull.  1984,  32:  2544 
    Google Scholar
  • 13a Yokoyama Y. Matsumoto T. Murakami Y. J. Org. Chem.  1995,  60:  1486 
    CrossrefGoogle Scholar
  • 13b Wang W. Xiong C. Yang J. Hruby VJ. Tetrahedron Lett.  2001,  42:  7717 
    CrossrefGoogle Scholar
  • 14 Liu R. Zhang P. Gan T. Cook JM. J. Org. Chem.  1997,  62:  7447 
    CrossrefPubMedGoogle Scholar
  • 15 Berthelot A. Piguel S. Le Dour G. Vidal J. J. Org. Chem.  2003,  68:  9835 
    CrossrefGoogle Scholar
  • 16a Elder AM. Rich DH. Org. Lett.  1999,  1:  1443 
    CrossrefGoogle Scholar
  • 16b Drury WJ. Ferraris D. Cox C. Young B. Lectka T. J. Am. Chem. Soc.  1998,  120:  11006 
    CrossrefGoogle Scholar
  • 17a Larock RC. Yum EK. J. Am. Chem. Soc.  1991,  113:  6689 
    CrossrefGoogle Scholar
  • 17b Larock RC. Yum EK. Refvik MD. J. Org. Chem.  1998,  63:  7652 
    CrossrefGoogle Scholar
  • 18a Ma C. Liu X. Li X. Flippen-Anderson J. Yu S. Cook JM. J. Org. Chem.  2001,  66:  4525 
    CrossrefGoogle Scholar
  • 18b Li X. Yin W. Srirama Sarma PVV. Zhao H. Ma J. Cook JM. Tetrahedron Lett.  2004,  45:  8569 
    CrossrefGoogle Scholar
  • 18c Castle SL. Srikanth GSC. Org. Lett.  2003,  5:  3611 
    CrossrefGoogle Scholar
  • 19 Link JT. In Organic Reactions   Vol 60:  Overman LE. John Wiley and Sons, Inc.; New Jersey: 2002.  p.157-534  
    Google Scholar
  • 20 Mori M. Chiba K. Ban Y. Tetrahedron Lett.  1977,  1037 
    CrossrefGoogle Scholar
  • 21 Odle R. Blevins B. Ratcliff M. Hegedus LS. J. Org. Chem.  1980,  45:  2709 
    CrossrefGoogle Scholar
  • 22 Chen C.-Y. Lieberman DR. Larsen RD. Verhoeven TR. Reider PJ. J. Org. Chem.  1997,  62:  2676 
    CrossrefGoogle Scholar
  • 23 Baran PS. Guerrero CA. Ambhaikar NB. Hafensteiner BD. Angew. Chem. Int. Ed.  2005,  44:  606 
    CrossrefGoogle Scholar
  • Prepared in four steps from glutamic acid in 80% overall yield according to Martin, see:
  • 25a Kokotos G. Padron JM. Martin T. Gibbons WA. Martin VS. J. Org. Chem.  1998,  63:  3741 
    CrossrefGoogle Scholar
  • 25b Padron JM. Kokotos G. Martin T. Markidis T. Gibbons WA. Martin VS. Tetrahedron: Asymmetry  1998,  9:  3381 
    CrossrefGoogle Scholar
  • 26 Typical Experimental Procedure. A solution of o-iodoaniline 3a (73.0 mg, 0.33 mmol), aldehyde 6 (104.0 mg, 0.30 mmol), and DABCO (101.0 mg, 0.9 mmol) and Pd(OAc)2 (3.4 mg, 0.015 mmol) in dry DMF (1.5 mL) was degassed. The reaction mixture was heated to 85 °C until the reaction was complete (usually 8-12 h). The reaction mixture was cooled to r.t. and was diluted with H2O. The aqueous phase was extracted with EtOAc and the combined organic phase was washed with brine, dried (Na2SO4), and evaporated to dryness under reduced pressure. Purification of crude product by flash column chromatography (silica gel, 20% EtOAc in heptane) provided the desired product 7 (101 mg, 81%; yellow oil). [α]D 23 -60.0 (c 1.00, CHCl3). IR (CHCl3): 3348, 2980, 2359, 1782, 1741, 1457, 1369, 1273, 1140, 1092, 852 cm-1. 1H NMR (300 MHz, CDCl3): δ = 8.45 (br s, 1 H), 7.58 (d, 1 H, J = 7.7 Hz), 7.34 (d, 1 H, J = 7.9 Hz), 7.15 (dt, 1 H, J = 1.2, 7.7 Hz), 7.09 (dt, 1 H, J = 1.2, 7.9 Hz), 6.98 (d, 1 H, J = 2.1 Hz), 5.20 (dd, 1 H, J = 4.7, 10.3 Hz), 3.77 (s, 3 H), 3.62 (dd, 1 H, J = 4.7, 14.9 Hz), 3.40 (dd, 1 H, J = 10.3, 14.9 Hz), 1.28 (s, 18 H). 13C NMR (75 MHz, CDCl3): δ = 171.1, 151.5, 136.3, 127.5, 123.2, 121.7, 119.2, 118.5, 111.2, 82.8, 58.9, 52.1, 27.6 (6 C), 25.8. MS (ESI): m/z = 441 [M + Na]. HRMS (ESI): m/z calcd for C22H30N2O6Na [M + Na]: 441.2002; found: 441.1975.
  • 27 Yadav JS. Reddy BVS. Reddy KS. Synlett  2002,  468 
    Artikel in Thieme ConnectGoogle Scholar
  • 28a Lizos DE. Murphy JA. Org. Biomol. Chem.  2003,  1:  117 
    CrossrefGoogle Scholar
  • 28b Kondo Y. Kojima S. Sakamoto T. J. Org. Chem.  1997,  62:  6507 
    CrossrefGoogle Scholar
  • 29 Sy W.-W. Synth. Commun.  1992,  22:  3215 
    CrossrefGoogle Scholar
  • For intramolecular Heck reaction involving a formal 5-endo cyclization on the enamine unit see:
  • 30a

    Ref. 21.
    Artikel in Thieme ConnectGoogle Scholar
  • 30b Iida H. Yuasa Y. Kibayashi C. J. Org. Chem.  1980,  45:  2938 
    Artikel in Thieme ConnectGoogle Scholar
  • 30c Kasahara A. Izumi T. Murakami S. Yanai H. Takatori M. Bull. Chem. Soc. Jpn.  1986,  59:  927 
    Artikel in Thieme ConnectGoogle Scholar
  • 30d Shaw KJ. Luly JR. Rappoport H. J. Org. Chem.  1985,  50:  4515 
    Artikel in Thieme ConnectGoogle Scholar
  • 30e Sakamoto T. Nagano T. Kondo Y. Yamanaka H. Synthesis  1990,  215 
    Artikel in Thieme ConnectGoogle Scholar
  • 30f Michael JP. Chang SF. Wilson C. Tetrahedron Lett.  1993,  34:  8365 
    Artikel in Thieme ConnectGoogle Scholar
  • 30g Koerber-Plé K. Massiot G. Synlett  1994,  759 
    Artikel in Thieme ConnectGoogle Scholar
  • 30h Latham EJ. Stanforth SP. Chem. Commun.  1996,  2253 
    Artikel in Thieme ConnectGoogle Scholar
  • 30i Watanabe T. Arai S. Nishida A. Synlett  2004,  907 
    Artikel in Thieme ConnectGoogle Scholar
24

l-Try was isolated in 10% yield under Baran’s modified conditions.